Butylated hydroxytoluene

First approved in 1984

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H24O
Molecular Weight	220.3505
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C

InChI

InChIKey=NLZUEZXRPGMBCV-UHFFFAOYSA-N

InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

HIDE SMILES / InChI

Molecular Formula	C15H24O
Molecular Weight	220.3505
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/inactive/butylated-hydroxytoluene-304.html | http://science.jrank.org/pages/1100/Butylated-Hydroxytoluene.html | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=172.115 | https://www.sciencedirect.com/science/article/pii/0013935182900020 | https://www.ncbi.nlm.nih.gov/pubmed/2988845

Butylated hydroxytoluene, commonly known as BHT, is an organic compound that is used in the food, cosmetic, and pharmaceutical industry as an antioxidant. BHT is a substituted derivative of phenol. BHT helps to prevent the formation of free radicals and oxidation. When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins. It may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms. The ability of oral BHT to lead to cancer is a controversial topic, but most food industries have replaced it with butylated hydroxyanisole (BHA). BHT was first used as an antioxidant food additive in 1954. BHT does have other commercial uses, as in animal feeds and in the manufacture of synthetic rubber and plastics, where it also acts as an antioxidant. The U.S. Food and Drug Administration has deemed that BHT is safe enough when used in limited concentrations. It currently permits its use in concentrations of about 0.01% to 0.02% in most foods. As an emulsion stabilizer in shortening, it may be used in a somewhat higher concentration, 200 parts per million.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19231207	Inhibitor 8504		630.0 nM [Ki]
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29295625 \| https://www.ncbi.nlm.nih.gov/pubmed/29205116 \| https://www.drugs.com/inactive/butylated-hydroxytoluene-304.html	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Asthma 244 Sources: https://clinicaltrials.gov/ct2/show/NCT02220673	Primary	Phase I 438	Unknown Approved Use Unknown
Herpes simplex infection 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2988845 https://www.webmd.com/vitamins-supplements/ingredientmono-1071-butylated%20hydroxytoluene.aspx?activeingredientid=1071&activeingredientname=butylated%20hydroxytoluene	Primary	Phase I 438	Unknown Approved Use Unknown
SUNBURN 11 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6db0332-58ed-4c82-a9dc-7fac621f1ac1	Inactive ingredient	Approved 8583	A-TEAM Approved Use USE HELPS PROTECT AGAINST SUNBURN Launch Date 2014

C_max

Value	Dose	Co-administered	Analyte	Population
0.09 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2606406/	0.5 mg/kg bw single, oral dose: 0.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		BUTYLATED HYDROXYTOLUENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
76 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2606406/	0.5 mg/kg bw single, oral dose: 0.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		BUTYLATED HYDROXYTOLUENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
15 % 4 times / day multiple, topical Highest studied dose Dose: 15 %, 4 times / day Route: topical Route: multiple Dose: 15 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2988845/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2988845/	Sources: https://pubmed.ncbi.nlm.nih.gov/2988845/
80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	Other AEs: Dysarthria, Lightheadedness... Other AEs: Dysarthria Lightheadedness Abnormality of gait Slurred speech Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/

AEs

AE	Dose	Population
Abnormality of gait	80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/
Dysarthria	80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/
Lightheadedness	80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/
Slurred speech	80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 910 P-gp 1741 CYP19A1 429 CYP1A2 2153 UMAT 30 CYP2C19 2057 rGSTA5 1	rCYP 3 UGT1A6 343 UGT1A9 423	CYP2B6 669

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671199#sid=170466785	inconclusive [IC50 27.5404 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671196#sid=144208291	inconclusive [IC50 40.0452 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743083#sid=144213719	inconclusive [IC50 43.2771 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671201#sid=144208291	inconclusive [IC50 44.9314 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1325#sid=11532869	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1326#sid=11532869	no
UMAT 30	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1326#sid=11532869	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671198#sid=144208291	yes [IC50 35.6903 uM]
CYP2B6 1160	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/18570159/	yes
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/18570159/	yes
rGSTA5 1	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/8923030/	yes

Drug as victim

Target	Modality	Activity
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
rCYP 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/3473001/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/588834#sid=17390001

PubMed

Title	Date	PubMed
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Quantitative analysis of early chemically-induced pulmonary lesions in mice of varying susceptibilities to lung tumorigenesis.	2006-09-28	16337739
New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents.	2006-08-15	16690318
Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species.	2006-07-01	16757516
Cytokine response to lipoprotein lipid loading in human monocyte-derived macrophages.	2006-06-26	16800873
Synthesis and antioxidant activity of [60]fullerene-BHT conjugates.	2006-06-02	16534828
Attenuation of the pulmonary inflammatory response following butylated hydroxytoluene treatment of cytosolic phospholipase A2 null mice.	2006-06	16443645
Evaluation of the antioxidant capacity of limonin, nomilin, and limonin glucoside.	2006-05-31	16719503
Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems.	2006-05-31	16719496
Cadmium-induced apoptosis in rat kidney epithelial cells involves decrease in nuclear factor-kappa B activity.	2006-05	16478757
Beta-catenin in the fibroproliferative response to acute lung injury.	2006-03	16272459
Does immune stimulation or antioxidant therapy reduce MNU-induced placental damage via activation of Jak-STAT and NFkappaB signaling pathways?	2006-02-02	16822543
Polypyrroles as antioxidants: kinetic studies on reactions of bilirubin and biliverdin dimethyl esters and synthetic model compounds with peroxyl radicals in solution. Chemical calculations on selected typical structures.	2006-01-06	16388613
Scavenging of dpph* radicals by vitamin E is accelerated by its partial ionization: the role of sequential proton loss electron transfer.	2005-10-27	16235930
[Activation of deoxyribonucleotide synthesis by radioprotectants and antioxidants as a key stage in formation of body resistance to DNA-damaging factors].	2005-10-11	16212261
Iron-ascorbic acid-induced oxidant stress and its quenching by paraoxonase 1 in HDL and the liver: comparison between humans and rats.	2005-10-01	16052486
Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry.	2005-10	15936080
Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats.	2005-08-15	16045903
Method development and validation for monitoring in vivo oxidative stress: evaluation of lipid peroxidation and fat-soluble vitamin status by HPLC in rat plasma.	2005-08-05	15990367
2,1,3-Benzothiadiazine derivatives: synthesis and screening versus PDE4 enzyme.	2005-08	15963514
[Determination of quercetin in apples by reversed-phase high performance liquid chromatography].	2005-05	16124576
Synthesis, biological evaluation and molecular modelling studies on benzothiadiazine derivatives as PDE4 selective inhibitors.	2005-02-15	15670947
TNF alpha potentiates glutamate neurotoxicity by inhibiting glutamate uptake in organotypic brain slice cultures: neuroprotection by NF kappa B inhibition.	2005-02-09	15713255
Synthesis and characterization of BHT-derived tert-butyl dendrons.	2005-02-04	15675869
Identification and antioxidant potential of flavonoids and low molecular weight phenols in olive cultivar chemlali growing in Tunisia.	2005-01-26	15656655
Single-site anionic polymerization. Monomeric ester enolaluminate propagator synthesis, molecular structure, and polymerization mechanism.	2005-01-26	15656635
Anticancer properties of propofol-docosahexaenoate and propofol-eicosapentaenoate on breast cancer cells.	2005	16168109
Inhibition of glutathione S-transferase P1-1 in mouse lung epithelial cells by the tumor promoter 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadienone (BHT-quinone methide): protein adducts investigated by electrospray mass spectrometry.	2004-12	15606144
Relative amounts of antagonistic splicing factors, hnRNP A1 and ASF/SF2, change during neoplastic lung growth: implications for pre-mRNA processing.	2004-12	15390079
Relative antioxidant capacities of propofol and its main metabolites.	2004-11	15248045
Vanadium-catalyzed sulfenylation of indoles and 2-naphthols with thiols under molecular oxygen.	2004-10-29	15497997
Mononuclear, five-coordinate lanthanide amido and aryloxide complexes bearing tetradentate (N2O2) Schiff bases.	2004-10-04	15446865
Optimization of a high-performance liquid chromatography system by artificial neural networks for separation and determination of antioxidants.	2004-10	15537075
Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation.	2004-09-22	15366830
Malondialdehyde, a lipoperoxidation-derived aldehyde, can bring about secondary oxidative damage to proteins.	2004-09	15472151
Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites.	2004-07	15172835
Inhibitory effects of organic acid salts on growth of Clostridium perfringens from spore inocula during chilling of marinated ground turkey breast.	2004-06-01	15135954
Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress.	2004-06	15153555
Effect of thiabendazole on some rat hepatic xenobiotic metabolising enzymes.	2004-06	15110098
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].	2004-05	15218738
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].	2004-04	15272608
Analysis of insecticidal Azadirachta indica A. Juss. fractions.	2004-03-17	15018062
Measurement of anti-HIV activity of marketed vaginal products and excipients using a PBMC-based in vitro assay.	2004-03	15076925
In vitro estrogenicity of resin composites.	2004-03	14981123
Mitochondrial permeability transition induced by reactive oxygen species is independent of cholesterol-regulated membrane fluidity.	2004-02-27	14987999
Cytotoxicity and apoptosis induction by butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT).	2004-02-26	14981915
A critical evaluation of the factors determining the effect of intramolecular hydrogen bonding on the O-H bond dissociation enthalpy of catechol and of flavonoid antioxidants.	2004-02-20	14978819
Monitoring of the antioxidant BHT and its metabolite BHT-CHO in German river water and ground water.	2004-02-05	14967516
Inhibition by butylated hydroxytoluene and its oxidative metabolites of DMBA-induced mammary tumorigenesis and of mammary DMBA-DNA adduct formation in vivo in the female rat.	1992-06	1500032
Haemorrhages due to defective blood coagulation do not occur in mice and guinea-pigs fed butylated hydroxytoluene, but nephrotoxicity is found in mice.	1992-02	1555799

Patents

Sample Use Guides

In Vivo Use Guide

The effect of topical therapy with 15% Butylated hydroxytoluene in mineral oil on the course of recurrent herpes simplex labialis was examined in 30 patients in a double-blind, placebo-controlled pilot study.

Route of Administration: Topical

In Vitro Use Guide

Butylated hydroxytoluene (BHT) inhibited lipoprotein oxidation by IC50 values of 0.8 uM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:47:35 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:35 GMT 2025`
Record UNII	1P9D0Z171K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Butylated hydroxytoluene

Common Name

English

BHT	Locators: FCC INCI Naming Organization: INCI Sources:

Preferred Name

English

Butylated hydroxytoluene [WHO-DD]

Common Name

English

BUTYLATED HYDROXYTOLUENE [USP-RS]

Common Name

English

INS NO.321

Code

English

BUTYLATED HYDROXYTOLUENE [II]

Common Name

English

BUTYLHYDROXYTOLUENE [EP MONOGRAPH]

Common Name

English

E-321

Code

English

PHENOL, 2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-

Systematic Name

English

BUTYLATED HYDROXYTOLUENE [VANDF]

Common Name

English

BUTYLATED HYDROXYTOLUENE (E 321)

Common Name

English

BUTYLATED HYDROXYTOLUENE [FHFI]

Common Name

English

BUTYLHYDROXYTOLUENE

Systematic Name

English

2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYLPHENOL

Systematic Name

English

BUTYLATED HYDROXYTOLUENE [IARC]

Common Name

English

BUTYLATED HYDROXYTOLUENE [MART.]

Common Name

English

BHT [FCC]

Common Name

English

2,6-DI-TERT-BUTYL-P-CRESOL

Common Name

English

KERABIT

Common Name

English

BUTYLATED HYDROXYTOLUENE [NF]

Common Name

English

4-METHYL-2,6-DITERTIARY-BUTYL-PHENOL

Common Name

English

2,6-DI-TERT-BUTYL-P-CRESOL2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-PHENOL

Systematic Name

English

NSC-6347

Code

English

BUTYLATED HYDROXYTOLUENE [HSDB]

Common Name

English

FEMA NO. 2184

Code

English

BUTYLATED HYDROXYTOLUENE [MI]

Common Name

English

INS-321

Code

English

2,6-DITERTIARY-BUTYL-P-CRESOL

Common Name

English

BUTYLATED HYDROXYTOLUENE [WHO-IP]

Common Name

English

BUTYLHYDROXYTOLUENUM [WHO-IP LATIN]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

22105